5-(4-Methoxy­phenyl)-4-methyl­thia­zole-2(3H)-thione

The mol­ecules of the title compound, C₁₁H₁₁NOS₂, form hydrogen-bonded dimers in the solid state. The amide H atom serves as hydrogen-bond donor and the thio­carbonyl S atom of a neighbouring mol­ecule serves as acceptor. The p-methoxy­phenyl substituent is tilted by 7.3 (5)° from the thia­zole-2(3H)-thione plane.

Key indicators

• Single-crystal X-ray study
• T = 299 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.041
• wR factor = 0.088
• Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found





Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction Limited, 2002); cell refinement: CrysAlis RED (Oxford Diffraction Limited, 2002); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON2003 (Spek, 1990, 2003) and ORTEP-3 (Farrugia, 1997, 2005); software used to prepare material for publication: SHELXL97.

4-Methyl-5-(p-methoxyphenyl)thiazole-2(3H)-thione

Crystal data

C11H11NOS2	Z = 2
Mr = 237.33	F(000) = 248
Triclinic, P1	Dx = 1.405 Mg m^−3
a = 6.227 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.360 (1) Å	Cell parameters from 1180 reflections
c = 11.624 (3) Å	θ = 2.7–22.9°
α = 76.00 (2)°	µ = 0.45 mm^−1
β = 78.40 (2)°	T = 299 K
γ = 75.05 (2)°	Plate, pale yellow
V = 561.03 (18) Å^3	0.52 × 0.28 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur (TM) Diffractometer with Sapphire CCD detector	2209 independent reflections
Radiation source: fine-focus sealed tube	1140 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
Rotation method data acquisition using ω scans	θmax = 26.4°, θmin = 4.1°
Absorption correction: analytical CrysAlis RED (Oxford Diffraction, 2002)	h = −7→7
Tmin = 0.801, Tmax = 0.974	k = −8→10
6413 measured reflections	l = −14→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 0.86	w = 1/[σ^2(Fo^2) + (0.031P)^2] where P = (Fo^2 + 2Fc^2)/3
2209 reflections	(Δ/σ)max = 0.023
139 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.19 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C2	0.3404 (5)	0.8042 (4)	0.4951 (3)	0.0343 (8)
C4	0.5019 (5)	0.9743 (4)	0.3272 (3)	0.0331 (7)
C5	0.6834 (5)	0.8472 (4)	0.3439 (3)	0.0349 (8)
C6	0.4686 (5)	1.1355 (4)	0.2350 (3)	0.0505 (9)
H6A	0.4999	1.1097	0.1564	0.061*
H6B	0.5686	1.2025	0.2408	0.061*
H6C	0.3160	1.1974	0.2489	0.061*
C7	0.9111 (5)	0.8196 (4)	0.2760 (3)	0.0338 (8)
C8	0.9844 (5)	0.9422 (4)	0.1819 (3)	0.0503 (10)
H8	0.8871	1.0465	0.1626	0.060*
C9	1.1974 (6)	0.9132 (4)	0.1165 (3)	0.0515 (9)
H9	1.2405	0.9965	0.0534	0.062*
C10	1.3465 (5)	0.7599 (4)	0.1450 (3)	0.0432 (9)
C11	1.2812 (5)	0.6387 (4)	0.2390 (3)	0.0449 (9)
H11	1.3808	0.5360	0.2599	0.054*
C12	1.0666 (5)	0.6699 (4)	0.3025 (3)	0.0435 (9)
H12	1.0253	0.5863	0.3660	0.052*
C13	1.7110 (6)	0.5913 (5)	0.0945 (3)	0.0815 (13)
H13A	1.6495	0.5035	0.0823	0.098*
H13B	1.7433	0.5658	0.1751	0.098*
H13C	1.8469	0.5986	0.0393	0.098*
N3	0.3161 (4)	0.9475 (3)	0.4121 (2)	0.0367 (7)
H3	0.187 (5)	1.024 (3)	0.414 (2)	0.044*
O1	1.5541 (4)	0.7469 (3)	0.0750 (2)	0.0655 (7)
S1	0.61319 (14)	0.69277 (10)	0.46866 (8)	0.0440 (3)
S2	0.14281 (14)	0.74163 (10)	0.60610 (8)	0.0483 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C2	0.0328 (19)	0.0301 (17)	0.0385 (19)	−0.0047 (15)	−0.0039 (15)	−0.0078 (16)
C4	0.0321 (19)	0.0321 (18)	0.0339 (19)	−0.0055 (16)	−0.0065 (16)	−0.0048 (15)
C5	0.0346 (19)	0.0359 (19)	0.0347 (18)	−0.0108 (16)	−0.0028 (15)	−0.0065 (15)
C6	0.040 (2)	0.047 (2)	0.052 (2)	−0.0006 (17)	−0.0061 (17)	0.0052 (18)
C7	0.0348 (19)	0.0337 (19)	0.0325 (19)	−0.0104 (17)	−0.0027 (16)	−0.0046 (15)
C8	0.037 (2)	0.049 (2)	0.052 (2)	−0.0004 (18)	−0.0030 (19)	0.0012 (18)
C9	0.041 (2)	0.050 (2)	0.047 (2)	−0.0050 (19)	0.0017 (18)	0.0090 (18)
C10	0.031 (2)	0.055 (2)	0.039 (2)	−0.0062 (18)	0.0007 (17)	−0.0075 (18)
C11	0.035 (2)	0.0335 (19)	0.054 (2)	0.0030 (16)	−0.0002 (18)	−0.0028 (17)
C12	0.038 (2)	0.038 (2)	0.045 (2)	−0.0114 (17)	0.0032 (18)	0.0042 (17)
C13	0.045 (2)	0.083 (3)	0.086 (3)	0.008 (2)	0.018 (2)	−0.008 (2)
N3	0.0280 (15)	0.0356 (17)	0.0412 (16)	−0.0028 (13)	−0.0013 (14)	−0.0052 (14)
O1	0.0383 (15)	0.0718 (18)	0.0581 (16)	0.0057 (14)	0.0133 (13)	0.0038 (13)
S1	0.0338 (5)	0.0381 (5)	0.0491 (6)	−0.0032 (4)	0.0021 (4)	−0.0001 (4)
S2	0.0380 (5)	0.0430 (5)	0.0535 (6)	−0.0069 (4)	0.0061 (5)	−0.0028 (5)

Geometric parameters (Å, º)

C2—N3	1.340 (3)	C8—H8	0.9300
C2—S2	1.679 (3)	C9—C10	1.385 (4)
C2—S1	1.720 (3)	C9—H9	0.9300
C4—C5	1.347 (4)	C10—C11	1.373 (4)
C4—N3	1.390 (3)	C10—O1	1.375 (3)
C4—C6	1.501 (4)	C11—C12	1.384 (4)
C5—C7	1.468 (4)	C11—H11	0.9300
C5—S1	1.758 (3)	C12—H12	0.9300
C6—H6A	0.9600	C13—O1	1.411 (3)
C6—H6B	0.9600	C13—H13A	0.9600
C6—H6C	0.9600	C13—H13B	0.9600
C7—C12	1.381 (4)	C13—H13C	0.9600
C7—C8	1.398 (4)	N3—H3	0.89 (3)
C8—C9	1.383 (4)
N3—C2—S2	126.9 (2)	C8—C9—H9	120.0
N3—C2—S1	107.9 (2)	C10—C9—H9	120.0
S2—C2—S1	125.27 (19)	C11—C10—O1	126.0 (3)
C5—C4—N3	112.3 (3)	C11—C10—C9	119.3 (3)
C5—C4—C6	131.5 (3)	O1—C10—C9	114.6 (3)
N3—C4—C6	116.2 (3)	C10—C11—C12	119.7 (3)
C4—C5—C7	131.3 (3)	C10—C11—H11	120.1
C4—C5—S1	109.3 (2)	C12—C11—H11	120.1
C7—C5—S1	119.3 (2)	C7—C12—C11	122.9 (3)
C4—C6—H6A	109.5	C7—C12—H12	118.5
C4—C6—H6B	109.5	C11—C12—H12	118.5
H6A—C6—H6B	109.5	O1—C13—H13A	109.5
C4—C6—H6C	109.5	O1—C13—H13B	109.5
H6A—C6—H6C	109.5	H13A—C13—H13B	109.5
H6B—C6—H6C	109.5	O1—C13—H13C	109.5
C12—C7—C8	116.0 (3)	H13A—C13—H13C	109.5
C12—C7—C5	121.5 (3)	H13B—C13—H13C	109.5
C8—C7—C5	122.5 (3)	C2—N3—C4	117.6 (3)
C9—C8—C7	122.0 (3)	C2—N3—H3	120.3 (18)
C9—C8—H8	119.0	C4—N3—H3	122.0 (18)
C7—C8—H8	119.0	C10—O1—C13	117.9 (3)
C8—C9—C10	120.0 (3)	C2—S1—C5	92.95 (15)
N3—C4—C5—C7	178.5 (3)	C9—C10—C11—C12	1.2 (5)
C6—C4—C5—C7	−1.8 (6)	C8—C7—C12—C11	−1.6 (4)
N3—C4—C5—S1	0.4 (3)	C5—C7—C12—C11	178.9 (3)
C6—C4—C5—S1	−179.9 (3)	C10—C11—C12—C7	0.0 (5)
C4—C5—C7—C12	−173.3 (3)	S2—C2—N3—C4	−179.5 (2)
S1—C5—C7—C12	4.7 (4)	S1—C2—N3—C4	0.5 (3)
C4—C5—C7—C8	7.3 (5)	C5—C4—N3—C2	−0.6 (4)
S1—C5—C7—C8	−174.8 (2)	C6—C4—N3—C2	179.6 (3)
C12—C7—C8—C9	2.2 (5)	C11—C10—O1—C13	5.0 (5)
C5—C7—C8—C9	−178.3 (3)	C9—C10—O1—C13	−176.7 (3)
C7—C8—C9—C10	−1.2 (5)	N3—C2—S1—C5	−0.3 (2)
C8—C9—C10—C11	−0.6 (5)	S2—C2—S1—C5	179.8 (2)
C8—C9—C10—O1	−179.0 (3)	C4—C5—S1—C2	−0.1 (2)
O1—C10—C11—C12	179.4 (3)	C7—C5—S1—C2	−178.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···S2^i	0.89 (3)	2.45 (3)	3.333 (3)	172 (2)

Symmetry code: (i) −x, −y+2, −z+1.